Title: Elliptone
CAS Registry Number: 478-10-4
CAS Name: 12,12a-Dihydro-8,9-dimethoxy[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one
Additional Names: derride
Molecular Formula: C20H16O6
Molecular Weight: 352.34
Percent Composition: C 68.18%, H 4.58%, O 27.25%
Literature References: Found in derris resins of low rotenone content. Isoln of naturally occurring (-)-form from Derris elliptica (Wall.) Benth., Leguminosae: Buckley, J. Soc. Chem. Ind. 55, 285T (1936); Harper, Chem. Ind. (London) 57, 1059 (1938); 58, 292 (1939); J. Chem. Soc. 1939, 1099; see also Meyer, Koolhaas, Rec. Trav. Chim. 58, 207 (1939). Structure: Harper, J. Chem. Soc. 1939, 1424; 1942, 593. Comparison with similar substances: Seiferle, Frear, Ind. Eng. Chem. 40, 683 (1948). Total synthesis of (±)-form: Fukami et al., Agric. Biol. Chem. 29, 82 (1965), C.A. 62, 13115e (1963). Synthesis of (-)-form from rotenone, q.v.: P. B. Anzeveno, J. Heterocycl. Chem. 16, 1643 (1979).
Properties: Needles from ethanol, mp 160° (Harper), also reported as mp 177-178° (Anzeveno). [a]D20 -18° (benzene); [a]D20 +55° (acetone).
Melting point: mp 160° (Harper); mp 177-178° (Anzeveno)
Optical Rotation: [a]D20 -18° (benzene); [a]D20 +55° (acetone) |